As a devastating series of cyberattacks struck the heart of the national-security establishment, the Feds set out to destroy the legendary hacker and radical anarchist by any means necessary

On a cold day in mid-December 2011, a hacker known as “sup_g” sat alone at his computer – invisible, or so he believed. He’d been working on the target for hours, long after the rest of his crew had logged off: an epic hack, the “digital equivalent of a nuclear bomb,” as it later would be described, on the servers of a Texas-based intelligence contractor called Strategic Forecasting Inc. Stratfor served as a sort of private CIA, monitoring developments in political hot spots around the world and supplying analysis to the U.S. security establishment.

A member of the online activist movement Anonymous, sup_g was part of a small team of politically motivated hackers who had breached Stratfor’s main defenses earlier that month – ultimately “rooting,” or gaining total access to, its main web servers. In them, they had found a cornucopia of treasure: passwords, unencrypted credit-card data and private client lists revealing Stratfor’s deep ties to both big business and the U.S. intelligence and defense communities. But perhaps the most lucrative find of all was Stratfor’s e-mail database: some 3 million private messages that exposed a wide array of nefarious and clandestine activities – from the U.S. government’s monitoring of the Occupy movement to Stratfor’s own role in compiling data on a variety of activist movements, including PETA, Wikileaks and even Anonymous itself.

And now, finally, it was done. Logging on to a secure Web chat, sup_g sent a message to a fellow activist. “We in business, baby,” he said. “It’s over with.”

One of the most radical and committed hackers in the shadowy world of Anonymous – a leaderless, nonhierarchical federation of activists with varying agendas – sup_g kept a low profile within the group, carefully concealing his real name and maintaining a number of aliases. That June, he had joined a new faction within Anonymous known as Operation Antisec, or #Antisec, which described itself as a “popular front” against the “corrupt governments, corporations, militaries and law enforcement of the world.” Though hundreds of activists may have frequented its internal communication channels, known as Internet relay chats, Antisec had less than a dozen core members: hackers, anarchists, free-speech activists and privacy crusaders, as well as “social engineers” – skilled manipulators whose talents lay in tricking even the most security-conscious into giving up their passwords or other data. The founder and most prominent member of Antisec was a bloviating, heavyset 29-year-old hacker, self-proclaimed revolutionary and social engineer known as “Sabu,” who had a special loathing, it seemed, for the intelligence industry. “Let us show them we can spy on them too,” he’d tweeted to his more than 35,000 followers in early December.

For three weeks, sup_g and his crew had worked steadily to ruin Stratfor, one of their biggest and richest targets yet. In addition to supplying geopolitical analysis to everyone from the Pentagon to the United Nations, the firm provided customized security services for leading companies like Raytheon and Dow Chemical, often compiling dossiers on activists and others viewed as threats to corporate profits. By Christmas – which Antisec dubbed “LulzXmas” for the “lulz,” or mocking enjoyment, they intended to have at Stratfor’s expense – the group had made off with more than 200 gigabytes of data. They then destroyed the company’s databases and defaced Stratfor’s website with a triumphant message promising a “week of mayhem” that would include posting the firm’s secrets online – some 860,000 names, e-mails and passwords, including several dozen belonging to top-secret operators whose identities were now leaked for the very first time. Antisec also planned to use the hacked credit cards to make donations to groups like CARE and the American Red Cross. As an added flourish, the group ended its communiqué with the full text of the influential French anarchist tract The Coming Insurrection. “It’s useless to wait . . . for the revolution,” the treatise reads. “The catastrophe is not coming, it is here.”

Three months later, on the evening of March 5th, 2012, more than a dozen federal law-enforcement officers broke down the door of a small brick house on the southwest side of Chicago and arrested Jeremy Hammond, a 27-year-old anarchist and computer hacker they believed to be sup_g. Six feet tall and lanky, dressed in a purple T-shirt and ratty trousers – a signature style one of his female friends noted was less Salvation Army than “the free box outside the Salvation Army” – Hammond looked more like a crusty punk than a computer nerd. In fact, he was both, as well as many other things: an inveterate “black hat” hacker, an irrepressible agitator and enemy of the “rich, ruling class” who identified with the ideas of the Weather Underground and considered the Occupy movement too tame.

Even before the arrest broadcast his name worldwide, Hammond was well-known in extreme-left circles. An early champion of “cyber-liberation,” he had been described by Chicago magazine at the age of 22 as an “electronic Robin Hood” after he was sentenced to two years in federal prison for hacking a conservative website and making off with 5,000 credit-card numbers, intending to charge donations to progressive causes. But unique within the hacking subculture, Hammond was also a real-life revolutionary: a “modern-day Abbie Hoffman,” in the words of his friend Matt Muchowski. He possessed a shrewd intelligence as well as a certain impulsivity – a fellow hacker referred to it as “urgency” – that had led to a long string of civil-disobedience arrests dating back 10 years, for offenses ranging from defacing a wall with anti-war slogans to banging a drum during a “noise demo” at the 2004 Republican National Convention in New York. (He later called his brief stint in the Tombs his “best prison experience.”) Hammond was even busted once, in 2005, for trying to join a protest, against a group of white supremacists in Toledo, Ohio. “They hadn’t even gotten out of the car when they were arrested,” says Muchowski, a Chicago union organizer who bailed Hammond out.

His arrest, the most prominent bust to date of a U.S. hacktivist, was also a major coup for the FBI. Before Hammond was locked up, Anonymous had engaged in a year-and-a-half-long hacking spree, waging a full-scale war against the “rich and powerful oppressors.” The group shut down the websites of the CIA, major banks and credit-card companies. They took up the cause of the Arab Spring by attacking the government websites of Libya, Tunisia and Egypt; they broke into computers belonging to NATO and the GEO Group, one of the world’s largest private prison corporations. They hacked defense contractor Booz Allen Hamilton – an attack, dubbed “Military Meltdown Monday,” that yielded 90,000 military and civilian e-mail accounts and passwords. They even attacked the FBI itself.

But none of these attacks had the political resonance of Stratfor. The computer breach not only cost the company millions, but focused worldwide attention on the murky world of private intelligence after Anonymous provided the firm’s e-mails to WikiLeaks, which has been posting them ever since. It was, by any estimate, an audacious hack – and one for which Hammond may face decades in prison.

Hammond, who has never admitted to any of the nine nicknames the government claims he operated under, has pleaded innocent to the Stratfor hack. But he has not disavowed his involvement with Anonymous, nor his desire to “push the struggle in a more direct action, explicitly anti-capitalist and anti-state direction,” as he wrote to me from Manhattan’s Metropolitan Correctional Center, where he has been held for the past eight months awaiting a bail hearing. Indeed, his hallmark as an activist has always been his revolutionary, militant rhetoric, for which he is unapologetic. “I have always made it clear that I am an anarchist-communist – as in I believe we need to abolish capitalism and the state in its entirety to realize a free, egalitarian society,” he wrote. “I’m not into watering down or selling out the message or making it more marketable for the masses.”

This unwavering commitment, one of Hammond’s greatest strengths, would also be what led to his undoing. He was always aware that betrayal was only a click away. “We know we’ll finish in prison,” says a hacker who worked with him. “Jeremy knew he was going to be raided, which is why he worked so quickly. He wanted people to remember him.” What Hammond never suspected was that his downfall would come at the hands of one of his closest and most trusted allies.

It’s an early-june morning at the Metropolitan Correctional Center, and Hammond walks into the small room usually reserved for lawyer-client conferences wearing a baggy brown prison jumpsuit meant for someone twice his size. In person, Hammond comes off as far less strident than he does on the page. He’s friendly, but cautious. After 10 years of activism, he is a seasoned veteran of jails and rough treatment at the hands of the police.

“Hey,” Hammond says calmly, “I’m Jeremy.” He’s a pale kid, nearly 28, with huge blue-green eyes, a wispy beard, and tattoos on each forearm – one, a tic-tac-toe-like symbol known as the “glider,” is an emblem of the open-source movement; the other, the shi hexagram from the I Ching, “can be interpreted as the leader of a people’s army,” he explains. He looks tired. “I’m on a terrorist watch list,” he tells me. “Hard to say what for, or how they monitor these terrorists.” He flashes me a wan smile that says “prison sucks.”

Since arriving here in March, Hammond has tried to keep busy teaching math to inmates who are studying for their GEDs, playing chess and reading anything he can get his hands on – most recently Love and Struggle, ex-Weatherman David Gilbert’s prison memoir. But being locked up is both a “dehumanizing” and also excruciatingly boring experience, he says. Aside from his lawyers, I am the only visitor he’s been permitted in three months.

Hammond was raised with his twin brother, Jason, in Glendale Heights, Illinois, a working-class town in the western suburbs of Chicago. His parents, Rose and Jack, never married, and when the twins were three, their mother moved out and later fell in love with a next-door neighbor, leaving the boys in the care of their father. According to Rose, who remained close to her sons, Jack Hammond was “a borderline genius” who had dropped out of high school to pursue a music career and had never wanted children “until the moment he laid eyes on the twins. Then his whole life was about them.”

Jack was part of the Chicago alternative scene of the 1980s that spawned iconic punk auteur Steve Albini. He raised his boys, who were nicknamed “Hanson” because of their long hair, to pursue whatever path appealed to them. Jason, a sensitive jokester, was a musician like his father. Jeremy, the quieter, more thoughtful of the two, was the schemer – the little boy who, at two, climbed to the top of the kitchen pantry to retrieve money he’d seen his mother hiding there. Jack, who earned about $35,000 a year as a guitar teacher and received child support from Rose, would later say he and the boys were “the world champs of living cheaply and well” in a do-it-yourself kind of way.

This didn’t always go over well in Glendale Heights – an area Hammond’s friend Matt Muchowski describes as “part Rust Belt, part Disney World. There are a ton of Walmarts and Niketowns, so what you get growing up is a pod-person mentality: The only job that’s there for you is at the mall.”